


prettiest boy

by bratboytyler



Category: Twenty One Pilots
Genre: Crossdressing, Fluff, M/M, it's all just fluff!! cute!!! and a tiny bit of angst i suppose
Language: English
Status: Completed
Published: 2015-12-15
Updated: 2015-12-15
Packaged: 2018-05-06 21:17:23
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,430
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5431061
Author URL: https://archiveofourown.org/users/bratboytyler/pseuds/bratboytyler
Summary: <blockquote class="userstuff">
              <p>Josh finally has the guts to buy and try on some dresses and skirts.</p>
            </blockquote>





	prettiest boy

**Author's Note:**

> twenty-one-lesters on tumblr asked me: "*Gentle whisper* Crossdressing anybody. No smut, just gentle fluff and cuteness. Plus the initial shock of finding out one person crossdresses but they're actually okay with it and fluff ensues. There's a prompt I guess." hope this is what you wanted!

Everyone who knew Josh, wouldn't immediately say he was a feminine dude. Sure, he's had pastel-coloured hair, and wore "make-up" on stage, but he still was a muscled, masculine guy. Gentle and quiet-spoken, a trait most people wouldn't say was a thing men could be, but masculine nonetheless. He just wasn't hyper-masculine. Thank god for that.  
But truth was, Josh wanted to explore his softer side more. Of course he knew that clothing and make-up don't have a gender at all, and you could wear anything you wanted, but in reality it wasn't as simple as in theory. A lot of people still judged you if you identified as male but still wanted to wear "girl clothes".

He's secretly snuck glances at the women's side of the stores he's been in while shopping with friends before, but has never actually bought something. Tyler was more brave in that. He's known to be shopping in the women's section of Forever 21 and H&M before, but those clothes weren't explecitely... feminine. Sure, you didn't see a guy in a floral robe every day, but Josh wanted to try all of it. Skirts and dresses, leggings, shoes with platform heels, cute necklaces and flower crowns. Maybe even nail polish?  
But never has he had the actual guts to buy the things he wanted.

Until now.  
After a quick raid through the nearest H&M without fitting anything because he was too anxious to get to the fitting rooms with his hands full of women's clothing, mumbling something about "my girlfriend" with red cheeks at the checkout while handing the bored-looking cashier their money, he had gotten back to his and Tyler's hotel room, out of breath and anxious. Tyler wasn't there yet, probably enjoying his day off with the crew, or wandering through whatever city they had stopped at today. He probably wouldn't be home until after dinner.  
Plenty of time to try on his new clothes, Josh figured. And probably also greatly regretting his decision and bringing them back to the store and never trying something like that out again.

"Well, here goes nothing," Josh quietly said to himself, pulling his snapback off his head and throwing it on his bed.

There was a life-sized mirror inside of the closet in the room, so he opened it and looked at himself. His image stared back.  
Josh stuck his tongue out to the mirror and turned around, grabbing for the first item he could reach; a white dress with red roses on it. He got rid of his other clothes except for his underwear, taking the dress in his hands and holding it in front of the mirror. It looked a little tight, especially for his rather broad chest...  
Fuck it, he thought, and stepped into the dress, after carefully opening the zipper on the back.  
After a few minutes of trying to get the dress over his chest, he realized he'd been right. The dress was too small for him, which was a shame, because he had really liked it when he first saw it in the shop.

A little disappointed, he stepped out of the dress, carefully folding it up and putting it back in the bag. This wasn't really going as he had planned, but there was still hope.

The next item was another dress. It was black and not as tight at the waist like the previous one had been, and it had a white collar. Josh had liked it because it looked like Wednesday Addam's dress.

He was a little more hopeful for this one when trying to slip it over his head. After some problems with trying to get his arms through the sleeves, the dress automatically fell over the rest of his body, stopping just above his knees. He flattened out the wrinkles, and when he was sure everything sat right, he looked up at the mirror.

For a moment, Josh was breathless. This was completely different from what he was used to wearing, but he looked so... cute?  
The dress concealed the fact that he didn't really have wide hips, and his broad chest wasn't extremely obvious.  
Josh giggled a bit, surprised at how much he liked the dress and how it made him look. He put a hand on his hip, turning and looking himself all up. Maybe he should have shaved his legs... then he would look even better.  
Next time, he promised himself. Today he would just see what fit before Tyler returned. He wasn't ready yet for others to find out he liked this.

The last item was actually an entire outfit he'd carefully put together. It consisted of a black croptop with a cat face drawn on it, a simple black skirt and leggings with pink roses on it.

Putting on the leggings weren't hard, since the fabric stretched easily over his legs. The croptop was maybe a bit tight at his shoulders, but he figured he could exchange it for a larger size when he went back to the shop to return the first dress.  
Josh was delighted to find out the skirt had a high waist, only stopping right under his belly button, so it wasn't too big. A skirt that rested on the hips would've been a bigger problem, since his hips weren't as wide as the average girl.

He hesistantly looked up, because what if the clothes didn't look good on him at all? What if he -

His train of thoughts was stopped by his mirrored image and he felt a smile creep on his face.  
Josh loved how he looked. He'd wanted to try things like this for so long, always envious of the girls with their floral leggings and skirts and cute rings and make-up. They all looked so pretty, and now so did he!  
Josh was overflowing with hapiness, and couldn't resist taking his phone from the discarted pants on the bed, unlocking it and opening the camera app. He probably wouldn't ever show anyone the photos, but he looked so lovely right now he had to snap some pictures.

Josh was so busy taking pictures of his outfit he didn't hear the door of the hotel room unlock and open, and he didn't hear the soft footsteps entering the room either.  
But he definitely heard Tyler's voice.

"Hey Josh, do you -" Tyler stopped abruptly when he saw his friend, freezing for a moment in his tracks.

Josh was sure his heart had stopped the moment Tyler froze. He could see him standing in the mirror, face expressionless.

"Tyler, I-I can - this isn't -," Josh started when he turned around, his heart now going so hard he was sure Tyler could hear it from the other side of the room, "listen, I'm -"

Josh whimpered and covered his face in his hands. He was close to crying and he didn't want Tyler to see him like this, not when he had just discovered he liked how he looked. He was sure Tyler would be disgusted by this and maybe wouldn't even want to be his friend anymore.

"Y-you can go away and we can pretend this never happened... I-I mean, if you still want to be my friend..." he mumbled from behind his hands.  
When Tyler didn't answer, he lowered his hands and looked up.

Tyler still hadn't moved.

"You... you like dressing up like this, Josh?" he asked in a soft voice.

See, he hates it, Josh thought, but he nodded anyway.

"It's not... like, you know, a sexual thing or something... I just like skirts and dresses and I know it's weird and you probably think I'm disgusting and -"

"Josh," Tyler interrupted him, carefully taking a step forward, "I... I don't think it's weird or anything."

"What?" Josh said in disbelief. Surely he misheard him.

"I don't mind... this," Tyler said, gesturing toward Josh, "It's okay. You shouldn't be ashamed."

"R-really?" Josh asked, again feeling like he was about to cry, but now from surprise and hapiness.

"Hey, Joshie, don't cry," Tyler said, closing the space in between them and hugging him tightly, "You look wonderful. I might even be a little jealous," he added.

Josh could barely believe this. He expected his best friend to turn on him, but he hadn't and it couldn't have gone better. He slid his arms around Tyler and hugged him too.

"Thank you," he whispered. Tyler let out a content hum.

"We should go shopping together once. Get matching outfits," he said.

Josh couldn't be happier. He had the best friend in the entire world.


End file.
